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Details

Stereochemistry ACHIRAL
Molecular Formula C17H19N2O5S.Na
Molecular Weight 386.398
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUMETANIDE SODIUM

SMILES

[Na+].CCCCNC1=C(OC2=CC=CC=C2)C(=CC(=C1)C([O-])=O)S(N)(=O)=O

InChI

InChIKey=QDFGOJHAQZEYQL-UHFFFAOYSA-M
InChI=1S/C17H20N2O5S.Na/c1-2-3-9-19-14-10-12(17(20)21)11-15(25(18,22)23)16(14)24-13-7-5-4-6-8-13;/h4-8,10-11,19H,2-3,9H2,1H3,(H,20,21)(H2,18,22,23);/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C17H19N2O5S
Molecular Weight 363.408
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including: http://www.rxlist.com/bumex-drug/side-effects-interactions.htm https://www.drugs.com/cdi/bumetanide.html http://www.wikidoc.org/index.php/Bumetanide_(oral)

Bumetanide is indicated for the treatment of edema associated with congestive heart failure, hepatic and renal disease, including the nephrotic syndrome. It blocks the reabsorption of sodium and fluid from the kidney's tubules. The most frequent clinical adverse reactions considered probably or possibly related to bumetanide are muscle cramps (seen in 1.1% of treated patients), dizziness (1.1%), hypotension (0.8%), headache (0.6%), nausea (0.6%) and encephalopathy (in patients with preexisting liver disease) (0.6%). One or more of these adverse reactions have been reported in approximately 4.1% of patients treated with Bumex (bumetanide). Lithium should generally not be given with diuretics (such as Bumex (bumetanide)) because they reduce its renal clearance and add a high risk of lithium toxicity. Bumex (bumetanide) may potentiate the effect of various antihypertensive drugs, necessitating a reduction in the dosage of these drugs.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
3.0 µM [IC50]
Target ID: Q9UP95|||O60632
Gene ID: 6560.0
Gene Symbol: SLC12A4
Target Organism: Homo sapiens (Human)
60.0 µM [IC50]
Target ID: Q9H2X9
Gene ID: 57468.0
Gene Symbol: SLC12A5
Target Organism: Homo sapiens (Human)
55.0 µM [IC50]
Target ID: Q13621
Gene ID: 6557.0
Gene Symbol: SLC12A1
Target Organism: Homo sapiens (Human)
4.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
BUMEX

Approved Use

Bumetanide Injection is indicated for the treatment of edema associated with congestive heart failure, hepatic and renal disease, including the nephrotic syndrome. Almost equal diuretic response occurs after oral and parenteral administration of bumetanide. Therefore, if impaired gastrointestinal absorption is suspected or oral administration is not practical, bumetanide should be given by the intramuscular or intravenous route. Successful treatment with bumetanide following instances of allergic reactions to furosemide suggests a lack of cross-sensitivity.

Launch Date

4.1523839E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
42 ng/mL
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BUMETANIDE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: FEMALE / MALE
food status: FASTED
111.38 ng/mL
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BUMETANIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
167.34 ng × h/mL
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BUMETANIDE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: FEMALE / MALE
food status: FASTED
258 ng × h/mL
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BUMETANIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.88 h
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BUMETANIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
5%
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BUMETANIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
3%
BUMETANIDE serum
Homo sapiens
population: HEALTHY
age: NEWBORN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
2 mg 2 times / day multiple, oral
Recommended
Dose: 2 mg, 2 times / day
Route: oral
Route: multiple
Dose: 2 mg, 2 times / day
Sources: Page: p.4
unhealthy, 14–18
n = 21
Health Status: unhealthy
Condition: Autism spectrum disorders
Age Group: 14–18
Sex: M+F
Population Size: 21
Sources: Page: p.4
Disc. AE: Hypokalemia, Anorexia...
AEs leading to
discontinuation/dose reduction:
Hypokalemia (moderate, 14.3%)
Anorexia (moderate)
Fatigue (moderate)
Polyuria (moderate, 4.8%)
Sources: Page: p.4
10 mg 1 times / day multiple, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: multiple
Dose: 10 mg, 1 times / day
Sources: Page: p.597
unhealthy, 22-72
n = 18
Health Status: unhealthy
Condition: Renal edema
Age Group: 22-72
Sex: M+F
Population Size: 18
Sources: Page: p.597
AEs

AEs

AESignificanceDosePopulation
Hypokalemia moderate, 14.3%
Disc. AE
2 mg 2 times / day multiple, oral
Recommended
Dose: 2 mg, 2 times / day
Route: oral
Route: multiple
Dose: 2 mg, 2 times / day
Sources: Page: p.4
unhealthy, 14–18
n = 21
Health Status: unhealthy
Condition: Autism spectrum disorders
Age Group: 14–18
Sex: M+F
Population Size: 21
Sources: Page: p.4
Polyuria moderate, 4.8%
Disc. AE
2 mg 2 times / day multiple, oral
Recommended
Dose: 2 mg, 2 times / day
Route: oral
Route: multiple
Dose: 2 mg, 2 times / day
Sources: Page: p.4
unhealthy, 14–18
n = 21
Health Status: unhealthy
Condition: Autism spectrum disorders
Age Group: 14–18
Sex: M+F
Population Size: 21
Sources: Page: p.4
Anorexia moderate
Disc. AE
2 mg 2 times / day multiple, oral
Recommended
Dose: 2 mg, 2 times / day
Route: oral
Route: multiple
Dose: 2 mg, 2 times / day
Sources: Page: p.4
unhealthy, 14–18
n = 21
Health Status: unhealthy
Condition: Autism spectrum disorders
Age Group: 14–18
Sex: M+F
Population Size: 21
Sources: Page: p.4
Fatigue moderate
Disc. AE
2 mg 2 times / day multiple, oral
Recommended
Dose: 2 mg, 2 times / day
Route: oral
Route: multiple
Dose: 2 mg, 2 times / day
Sources: Page: p.4
unhealthy, 14–18
n = 21
Health Status: unhealthy
Condition: Autism spectrum disorders
Age Group: 14–18
Sex: M+F
Population Size: 21
Sources: Page: p.4
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer










Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
modest [IC50 348 uM]
yes [IC50 0.75 uM]
yes [IC50 7.6 uM]
yes [IC50 77.5 uM]
Drug as victim
PubMed

PubMed

TitleDatePubMed
Functional comparison of the K+-Cl- cotransporters KCC1 and KCC4.
2000 Sep 29
External Cl(-)-dependent formation of watery vacuoles by long-term hypotonic shock in 3T3-L1 cells.
2001
Diuretic therapy and resistance in congestive heart failure.
2001
Effect of chloride channel blockers on anti-IgE-stimulated histamine and IL-4/IL-13 release from human basophils.
2001 Apr
Insulin increases the turnover rate of Na+-K+-ATPase in human fibroblasts.
2001 Apr
Effects of thiazide- and loop-diuretics, alone or in combination, on calcitropic hormones and biochemical bone markers: a randomized controlled study.
2001 Aug
"Avian-type" renal medullary tubule organization causes immaturity of urine-concentrating ability in neonates.
2001 Aug
Protection of ischemic myocardium in diabetics by inhibition of electroneutral Na+-K+-2Cl- cotransporter.
2001 Aug
Insulin-independent, MAPK-dependent stimulation of NKCC activity in skeletal muscle.
2001 Aug
Cl(-)-dependent secretory mechanisms in isolated rat bile duct epithelial units.
2001 Aug
Contractile regulation of the Na(+)-K(+)-2Cl(-) cotransporter in vascular smooth muscle.
2001 Aug
Optical method for quantifying rates of mucus secretion from single submucosal glands.
2001 Aug
Regional differences in ciliary epithelial cell transport properties.
2001 Aug 1
Contribution of the Na-K-Cl cotransporter on GABA(A) receptor-mediated presynaptic depolarization in excitatory nerve terminals.
2001 Aug 15
Cisplatin-induced apoptosis of mesothelioma cells is affected by potassium ion flux modulator amphotericin B and bumetanide.
2001 Aug 15
An integrative, in situ approach to examining K+ flux in resting skeletal muscle.
2001 Dec
Growth factors stimulate the Na-K-2Cl cotransporter NKCC1 through a novel Cl(-)-dependent mechanism.
2001 Dec
Adrenergic receptor activated ion transport in human fetal retinal pigment epithelium.
2001 Jan
Hepatic uptake of synthetic chlorogenic acid derivatives by the organic anion transport proteins.
2001 Jan
Liquid and ion transport by fetal airway and lung epithelia of mice deficient in sodium-potassium-2-chloride transporter.
2001 Jul
Na+-K+-Cl- cotransporter in rat focal cerebral ischemia.
2001 Jun
cAMP-dependent fluid secretion in rat inner medullary collecting ducts.
2001 Jun
Na+ reabsorption in cultured rat epididymal epithelium via the Na+/nucleoside cotransporter.
2001 Mar
Inhibition of Na(+)/K(+)-atpase by endothelin-1 in human nonpigmented ciliary epithelial cells.
2001 Mar
HCO3- potentiates the cAMP-dependent secretory response of the human distal colon through a DIDS-sensitive pathway.
2001 May
Diverging effects of 5-HT3 receptor antagonists ondansetron and granisetron on estramustine-inhibited cellular potassium transport.
2001 May
Pulmonary oedema after ophthalmic regional anaesthesia in an unfasted patient undergoing elective surgery.
2001 May
Role of renocortical cyclooxygenase-2 for renal vascular resistance and macula densa control of renin secretion.
2001 May
Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney.
2001 May
Localization of a Na(+)-K(+)-2Cl(-) cotransporter in the rabbit lens.
2001 Nov
Role of Cl- current in endothelin-1-induced contraction in rabbit basilar artery.
2001 Nov
Vacuolation induced by VacA toxin of Helicobacter pylori requires the intracellular accumulation of membrane permeant bases, Cl(-) and water.
2001 Nov 23
Ion transport and ligand binding by the Na-K-Cl cotransporter, structure-function studies.
2001 Oct
Mechanism(s) of chloride transport in human distal colonic apical membrane vesicles.
2001 Oct
Quantitative determination of the loop diuretic bumetanide in urine and pharmaceuticals by high-performance liquid chromatography with amperometric detection.
2001 Oct
Indirectly gated Cl(-)-dependent Cl(-) channels sense physiological changes of extracellular chloride in the leech.
2001 Oct
Contribution of the Na(+)-K(+)-2Cl(-) cotransporter (NKCC1) to transepithelial transport of H(+), NH(4)(+), K(+), and Na(+) in rat outer medullary collecting duct.
2002 Apr
Chloride transport in rabbit esophageal epithelial cells.
2002 Apr
Manipulation of chloride flux affects histamine-induced contraction in rabbit basilar artery.
2002 Apr
Activation of ion secretion via proteinase-activated receptor-2 in human colon.
2002 Feb
Intrinsic optical signals in the rat optic nerve: role for K(+) uptake via NKCC1 and swelling of astrocytes.
2002 Feb
Basolateral PAR-2 receptors mediate KCl secretion and inhibition of Na+ absorption in the mouse distal colon.
2002 Feb 15
Effects of butyrate on active sodium and chloride transport in rat and rabbit distal colon.
2002 Feb 15
Cyclic AMP-dependent Cl secretion is regulated by multiple phosphodiesterase subtypes in human colonic epithelial cells.
2002 Jan 15
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Parenteral Administration: The usual initial dose is 0.5 to 1 mg intravenously or intramuscularly. Intravenous administration should be given over a period of 1 to 2 minutes. If the response to an initial dose is deemed insufficient, a second or third dose may be given at intervals of 2 to 3 hours, but should not exceed a daily dosage of 10 mg.
The usual total daily dosage of Bumetanide is 0.5 mg to 2 mg and in most patients is given as a single dose.
Route of Administration: Other
10 uM of bumetanide reduced amplitude and frequency of ictal-like events (ILE) induced by 8.5 mM K(+), but it increased the frequency of ILE induced by 1 microM kainate.
Substance Class Chemical
Created
by admin
on Thu Jul 06 18:37:45 UTC 2023
Edited
by admin
on Thu Jul 06 18:37:45 UTC 2023
Record UNII
1QC8KM52D1
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BUMETANIDE SODIUM
Common Name English
BUMETANIDE SODIUM SALT
Common Name English
SODIUM 3-(AMINOSULFONYL)-5-(BUTYLAMINO)-4-PHENOXYBENZOATE
Systematic Name English
BENZOIC ACID, 3-(AMINOSULFONYL)-5-(BUTYLAMINO)-4-PHENOXY-, SODIUM SALT (1:1)
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID60182634
Created by admin on Thu Jul 06 18:37:45 UTC 2023 , Edited by admin on Thu Jul 06 18:37:45 UTC 2023
PRIMARY
CAS
28434-74-4
Created by admin on Thu Jul 06 18:37:45 UTC 2023 , Edited by admin on Thu Jul 06 18:37:45 UTC 2023
PRIMARY
ECHA (EC/EINECS)
249-015-6
Created by admin on Thu Jul 06 18:37:45 UTC 2023 , Edited by admin on Thu Jul 06 18:37:45 UTC 2023
PRIMARY
FDA UNII
1QC8KM52D1
Created by admin on Thu Jul 06 18:37:45 UTC 2023 , Edited by admin on Thu Jul 06 18:37:45 UTC 2023
PRIMARY
PUBCHEM
23696786
Created by admin on Thu Jul 06 18:37:45 UTC 2023 , Edited by admin on Thu Jul 06 18:37:45 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE